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MLB Offseason: Which Stars Will Be the Next $100 Million Men?

As the MLB offseason gets underway, several players could be in line to earn a $100 million payday.

MLB Offseason: Which Stars Will Be the Next $100 Million Men?
Will Robinson Cano become the first $300 million man in MLB? Photo courtesy Keith Allison via Creative Commons license.

Just two days after the Boston Red Sox beat the St. Louis Cardinals to capture the World Series title, the focus in major league baseball now turns to the offseason, more commonly known as the Hot Stove League.

It’s actually a league in itself, except that the players are pawns, and management steps to the plate. General managers, scouting directors, player personnel chiefs and owners will start to work on upgrading their team rosters. It’s during the winter months that they earn their keep. And it’s their decisions that will likely dictate the direction of their teams as well.

Free agency is a big part of offseason planning, and while this year’s crop of free agents isn’t considered elite, there are some intriguing options at the top of the list who will command big money, either from the teams they’re currently with or from potential new employers.

The $100 million contract is now considered the standard for the elite players, so we’ll take a look at just who could command that kind of money in today’s market.


Robinson Cano, New York Yankees

It almost seems unfathomable that New York Yankees second baseman Robinson Cano could actually don another uniform next season. But he is without question the top prize in this winter’s free-agent pool, and the $100 million mark might pale in comparison to what he could receive.

In fact, the total value of his next contract could be triple that number.

That was the number that was bandied about last September, and if achieved would make Cano the highest-paid player in the history of MLB, surpassing Alex Rodriguez’s 10-year, $275 million contract signed back in 2007.

Can Cano actually get that kind of money? From the Yankees, it’s doubtful. They supposedly offered a seven-year, $161 million contract earlier this year. In addition, the Yankees are looking to get under the $189 million luxury tax threshold by the start of the 2014 season. Signing Cano for upwards of $30 million per season would be a major stumbling block in achieving that goal.

That, however, is just a goal. Considering their disappointing third-place finish in the AL East and missing the playoffs for just the second time in 19 seasons, money will be spent to avoid that same fate again. But spending $300 million for Cano’s services won’t be an option. Cano could get over $200 million from either the Yankees or another team looking to make a huge splash, but for now, Rodriguez’s record contract will likely continue to be the standard-bearer.


Jacoby Ellsbury, Boston Red Sox

Fresh off a World Series win, Boston Red Sox center fielder Jacoby Ellsbury will be looking to get paid on the free-agent market. The $100 million mark for the speedy 30-year-old is definitely within reach. The Red Sox would probably like to bring him back, but if the price tag goes beyond $100 million, they’ll likely back away and give the job to center fielder-in-waiting Jackie Bradley, Jr.

Ken Rosenthal of went on local Boston radio station WEEI last month and gave his opinion on where he believes Ellsbury will sign.


It makes sense, considering Ellsbury is from the Northwest, and the Mariners desperately need a quality center fielder.

There’s also a faction of experts who believe that Ellsbury could sign a contract similar to the deal signed last year by B.J. Upton, for five years and somewhere around $75 million, but that could be just a starting point for negotiations as well. That’s a price tag that the Red Sox could well be interested in. However, with Scott Boras as his agent, less is never an option.


Shin-Soo Choo, Cincinnati Reds

Center fielder Shin-Soo Choo put together a nice season with the Cincinnati Reds, hitting 21 home runs with a .423 on-base percentage. That’s pretty much what any manager would love to have from their leadoff hitter.

Choo will also be looking to get paid this winter as he enters the free-agent market for the first time. And care to guess who his agent is? Yes, that would be one Scott Boras.

Boras believes that Choo is worth at least $100 million.

"As a custom of the industry, prognostications by executives this time of year are dramatically divergent from the real market," Boras said in a phone interview with Jon Heyman of "I don't think anyone correctly predicted what Jayson Werth or Carl Crawford got."


Clayton Kershaw, Los Angeles Dodgers

Los Angeles Dodgers southpaw Clayton Kershaw is not a free agent as of yet, but could be signing a long-term extension with the Dodgers this winter. That number will easily eclipse $100 million and will likely make him the highest-paid pitcher in MLB history.

In fact, Kershaw could be the one who eclipses the $300 million mark, not Robinson Cano.


This is a deal that will be a done-deal by the end of the winter, and Kershaw, who is the frontrunner for this year’s NL Cy Young Award, will walk away with a contract that exceeds that of anyone else in baseball.

You can bank on that. 

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